ST. PETERSBURG – The Red Sox achieved step one of their goal by punching their ticket to the playoffs on Sunday.
Now, they have six regular-season games left to prepare for what is to come.
One big objective will be to get postseason baseball back to Fenway Park for the first time since 2021. After losing in three games in the 2025 AL Wild Card Series to the Yankees at Yankee Stadium, the ending felt too abrupt.
It has already been an improbable turnaround for the Red Sox, surging from 14 games under .500 on June 25 and getting to the postseason. There is a belief within the clubhouse that more magic can happen.
“I think we can make a run,” said rookie lefty Payton Tolle. “I think we’ve got the guys. I think we can get hot. We’re just going to continue to play the way that we play. That team baseball we’ve been playing. You play to get to the postseason and to give yourself a shot to go to the World Series.”
Without further ado, here are some key talking points heading into the playoffs.
What could the postseason roster look like?
C: Adley Rutschman, Connor Wong
1B: Willson Contreras
2B: Nick Sogard
SS: Trevor Story
3B: Caleb Durbin
UTIL: Isiah Kiner-Falefa, Mickey Gasper
OF: Jarren Duran, Ceddanne Rafaela, Wilyer Abreu, Braiden Ward
DH: Roman Anthony, Jahmai Jones
SP: Sonny Gray, Ranger Suarez, Payton Tolle
Bullpen: Aroldis Chapman, Garrett Whitlock, Tyron Guerrero, Erik Miller, Greg Weissert, Brayan Bello, Jake Bennett, Garrett Crochet, Tanner Houck
The most intriguing decision for the position-player roster surrounds whether to add Ward, who set the Triple-A Worcester record with 61 stolen bases this season, as a pinch-running specialist. Dave Roberts, anyone?
The bullpen situation also bears watching. Considering that Crochet hasn’t pitched since April 25 and Houck’s next appearance will be his first in the Majors since 2025, the club will monitor how both rehabbers are throwing before finalizing the roster. This could influence if the club carries Bennett as a reliever. Jovani Morán is another option from the left side.
When does the postseason begin?
For the Red Sox, the fun starts on Sept. 29, when interim manager Chad Tracy’s club participates in an AL Wild Card Series, with all games in the best-of-three series to be played on the road. The Yankees, unless they improbably take the AL East from the Rays, will be the Red Sox opponent in what will be yet another chapter in the richest rivalry in baseball. The only other scenario that can stave off another rivalry match would be the Red Sox slipping to the No. 6 seed. They lead the current No. 6 seed, the White Sox, by four games.
How have the Red Sox performed against the Yankees this season?
Last year, Boston’s hopes of getting a playoff game at Fenway Park for the first time since ‘21 ended when the team lost Game 3 of the Wild Card Series to … the Yankees in the Bronx. So, yes, this would be a rematch between the rivals. In a form befitting the rivalry, the regular-season series swayed back and forth, with New York ultimately taking seven of the 13 head-to-head encounters.
The Yankees swept the Red Sox at Fenway from April 21-23 in what wound up being Alex Cora’s last home series managing Boston. Fast forward to the Bronx from June 5-7, and the sides split, with the middle game getting postponed due to rain. For the Red Sox, their entire season started to turn around with a four-game sweep at Fenway from June 25-28. And for the Yankees, home field for this potential series was essentially wrapped up when they took three out of four from the Sox at the end of August to clinch the season series.
Will Aaron Judge be active for the Wild Card Series?
Judge’s potential participation in the series will be a huge focal point. The Yankees’ captain, limited to 66 games this season, was recently placed on the injured list again with a right calf strain. Though the Yankees have played more games without Judge than with him, his absence could make a difference for Boston.
What happens in the unlikely scenario the Red Sox slip from the No. 5 seed to the No. 6 spot?
In that case, the Red Sox would play the division champion with the worst record, which at this point would be whoever emerges victorious in a shaky AL West.
Which health situations should be monitored as the regular season winds down?
Where to start? There are many to choose from.
Contreras suffered a badly bruised knuckle between his right ring finger and pinkie when he was hit by a pitch on Sept. 17. He admitted he will be out for “days,” but hopes to be back before the postseason. It was a good sign that Contreras was able to grip a bat and take some swings on Sunday.
All eyes will be on Crochet to see if it’s possible to activate him for the playoffs as a reliever even though he hasn’t pitched since April 25 due to left shoulder inflammation.
Chapman has been dealing with a lat injury that has kept him out of action since Sept. 13, but is confident he’ll return during the final homestand.
Rafaela, the Red Sox's All-Star center fielder, has been out since Sept. 3 with a right quadriceps strain but should return before the regular season ends.
How does the rotation line up for the Red Sox?
If not for the near season-long loss of Crochet to this point, the Game 1 starter wouldn’t be in question. Tracy reordered his rotation for the upcoming series, going with Tolle on Tuesday against the Guardians, followed by Gray on Wednesday and Suarez on Thursday. Could this be the same order the Sox open the playoffs with? Tracy isn’t ready to reveal those plans yet.
How much postseason experience does Boston’s projected roster have?
Contreras and Chapman both won World Series rings while playing for the 2016 Cubs. Chapman added another one with the Rangers in ‘23. Kiner-Falefa was with Toronto last season, meaning he got to play in the epic Dodgers-Blue Jays World Series, losing one of the most dramatic Game 7s ever.
Rutschman played in five postseason games during his time with the Orioles, but none beyond the Division Series. Several players in Boston’s young core got their first taste of postseason experience last year in Abreu, Rafaela and Duran. Durbin went to the NLCS with the Brewers in ‘25. Houck and Whitlock are the only players remaining on the Boston team that came two wins from making the World Series in ‘21. Veteran shortstop Story had a solid Wild Card Series in the Bronx last year.
Suarez (4-1, 1.48 ERA in 11 outings, eight starts) had his share of October moments in Philadelphia, and Gray has a 3.26 ERA in six career playoff starts.